The Complete Transformation Of Kimberly Guilfoyle's Face

In 2025, The Daily Beast published a piece hinting that Kimberly Guilfoyle, among other women in the Trump government, had changed her sense of style out of some sort of loyalty to President Donald Trump and his campaign. In a piece titled, "Usha Vance is about to transform into a Trumpian trad wife," writer, Joanna Coles, described the ways in which several women had transformed their looks in response to their relationships to different men within the Trump empire. Apparently, Guilfoyle was one such woman. After all, she dated Donald Trump Jr., and as the article states, "Guilfoyle was once a lawyer, too. Now she's a Republican adviser with tunnel cleavage and heavy dark eye makeup that would make even Cleopatra say, 'Honey, hold the kohl.'"

While this story of Kimberly Guilfoyle's Trumpian fashion transformation may be tempting to believe, the reality is actually much more complicated than that. In fact, Guilfoyle embraced beauty-queen makeup long before she met Donald Trump Jr. She might have even undergone several surgical enhancements almost a decade before the "Make America Great Again" movement even existed. Although it is true that Guilfoyle has changed her face a lot over the years, it seems that this transformation has occurred in tandem with her professional evolution rather than her relationships. From her time as a public figure in San Francisco to her tenure as a media consultant to a nominee for the American ambassador to Greece, Guilfoyle has allowed her face to reflect her position. 

These days, Kimberly Guilfoyle is known as a former Fox News media personality, Donald Trump Jr.'s ex-girlfriend, and President Donald Trump's pick as ambassador to Greece. But back in the late 1960s, she was an adorable baby who was loved by her parents. Indeed, around the time of her birth in March 1969, the future media personality's mother, Mercedes Gerena, and her father, Anthony Guilfoyle, splurged on a formal family photo. The shot — which Kimberly later shared on Instagram — shows the proud parents staring at the camera with their baby on Mercedes' lap. Kimberly was, of course, as cute as a button with round cheeks and a full head of hair. Her face reveals a certain amount of curiosity as she stares at the camera.

Although it's hard to look at this old photo and imagine the stunning transformation that Kimberly Guilfoyle would one day undergo, it is easy to pinpoint the resemblance between the public figure and her mother. Like Kimberly, Mercedes boasted full lips and a square jaw. Her mother also had prominent cheekbones that were clearly passed down to her daughter. Even though Kimberly Guilfoyle has long inspired plastic surgery rumors, her mother's traits show that many of her features were actually inherited down the maternal line. 

Although the adult Kimberly Guilfoyle looks a whole lot like her mother, the young Guilfoyle actually took after her father. Grainy family photos from the 1970s show that the media personality resembled her dad in more ways than one. In an old childhood picture posted on Guilfoyle's Instagram, she's hugging her father and smiling at the camera. The cheek-to-cheek shot shows that Guilfoyle inherited her pointy nose and bright smile from her dear old man.

Interestingly, a family resemblance is not the only thing that the media personality got from the paternal side of her family. Guilfoyle's mother died when she was only 10 years old. Therefore, her father stepped up and raised her alone. As Guilfoyle shared in the caption of the aforementioned Instagram post, "After we lost her, you raised Anthony and me with endless love and strength ... You'll always be my hero."

During the years when Guilfoyle was cared for by her father, she watched him pass down some of his most beloved values. These included bravery, courage, and patriotism — ideals that Guilfoyle says she follows to this day. As she shared in the caption of a separate Instagram post, "From an early age, my father inspired and taught me to always stand up for myself, my values and my country. I still remember my father saying: Be more afraid of the fear that hinders [you] than the fear of asking, always be your best advocate."

As Kimberly Guilfoyle moved into her adult years, her life changed completely. While completing her undergraduate degree at the University of California, Davis, she realized that she wanted to become a lawyer. Although she was accepted into the University of San Francisco School of Law, Guilfoyle's future in the legal world was far from guaranteed. After all, her tuition and living expenses were not exactly free. Motivated to make ends meet, Guilfoyle decided to try her hand at modeling. As she would later tell People, "I knew I wanted to go to law school and it ended up being a great way to pay for it. I modeled everything from clothes, swimwear and lingerie, including Victoria's Secret!"

Although the modeling world has the reputation for emphasizing makeup and plastic surgery, Guilfoyle apparently avoided these enhancers during her early career. She even posted an old headshot on Instagram — revealing that she was accustomed to embracing an all-natural, makeup-free look. 

Because of this, her face looked young, fresh, and totally clean. Reflecting on these days with People, Guilfoyle remembered the lessons she learned, not just the clothes she wore. "I met an incredible number of interesting people through modeling and really learned a lot about self-confidence and self-worth," she explained.

Kimberly Guilfoyle may have avoided makeup in her old modeling headshots, but that doesn't mean she maintained this natural look for long. After graduating from law school, she chose to go into public life, first as a prosecutor in San Francisco and eventually an Assistant District Attorney. During this time, she fell in love with future Governor of California Gavin Newsom, who was then hoping to become the mayor of San Francisco. The pair walked down the aisle in 2001, and Newsom became mayor three years later — making Guilfoyle the first lady of San Francisco.

For Guilfoyle, taking on these roles in the public eye was a really big deal. No longer was she a typical law student — she was an important political figure. As such, photos show Guilfoyle wearing subtle, first-lady makeup during this time period. One shot shows her at a party with Newsom. On this occasion, she dressed up her look with simple eyeshadow, lipstick, lip gloss, and a solid layer of foundation. As much effort as Guilfoyle invested into her face, however, she was known for her personality. Newsom himself told SFGate in 2001, "I can also say that Kimberly is the only person I have ever known in my life who gets more and more attractive with every day that passes. And that comes from inside, obviously."

Just because Kimberly Guilfoyle took on a public role during her tenure in the district attorney's office doesn't mean that she always went for the most glamorous looks. In 2004, she attended several events in what appeared to be semi-professional attire. This was especially true at the GLAAD Media Awards in New York City. For this event, she wore a strappy black dress that kept things cool. Her face matched the overall feel of her look as she wore an adorable pair of glasses at the podium.

Although the choice to wear glasses or not may seem small, framing your face with a pair of spectacles can fully transform the way others perceive you. Writing for Psychology Today, Susan Krauss Whitbourne, PhD, ABPP, explained that this accessory really can make you look smarter. "People with glasses look like they read more; hence, they are [viewed as] more intelligent," the expert shared. Whitbourne also noted that glasses can impact the way others perceive your moral character, writing, "You may look more trustworthy if you're wearing glasses with rims." In that sense, Guilfoyle's choice of accessory would have framed her face in a way that was helpful for her political career. Not only did her glasses make her look sharper, but they also made her seem like a more ethical person.

Although Kimberly Guilfoyle and Gavin Newsom remained married for a time, the political power couple was not meant to last. The pair divorced in 2006 and Guilfoyle went on to marry Eric Villency that very May. Just five months after tying the knot in a romantic Barbados ceremony, Villency and Guilfoyle welcomed their son, Ronan Villency, in 2006. Shortly after giving birth, Kimberly Guilfoyle rocked a rare no-makeup look that enhanced her beauty in a throwback photo she posted on social media.

As revealed in a photo of this moment — which Guilfoyle later shared on Instagram — the media personality apparently kept her face completely natural. She wore no visible eyeliner or eyeshadow, and the small freckles that we can see on her cheeks suggest that she forewent foundation as well. This image shows that Guilfoyle did not dress up her countenance for those first few moments of maternity. Instead, she decided to spend that time bonding with her new son.

The beginnings of Kimberly Guilfoyle's career may have been marked by a number of natural looks, but that doesn't mean she embraced those for long. In 2005, Guilfoyle began hosting "Both Sides" on CourtTV — allowing her to transform from a political figure to a media one. As Guilfoyle began to spend more and more time in front of the cameras, rumors of potential plastic surgeries began to pop up all around her. To get to the bottom of the hearsay, The List reached out to Dr. Raja Mohan, a board-certified plastic surgeon based in Dallas, Texas. Based on what Dr. Mohan told us, it's very possible that Guilfoyle underwent a few procedures around this time.

Pointing to a photograph of Guilfoyle at the premiere of the 2007 film "Sleuth" in New York City, the surgeon told us, "The most notable differences appear in the contour of the jawline and neck, which are sharper and more defined ... This can be achieved through a lower facelift or neck lift, sometimes combined with liposuction under the chin to remove excess fat and tighten the skin." In other words, Guilfoyle potentially sought surgical interventions to help her achieve a younger look. She also appeared to increase the amount of makeup on her face, applying copious amounts of black eyeliner and a particularly shiny brand of lipgloss. 

As Kimberly Guilfoyle's media career took off, she piled more makeup on. In 2011, the former Democratic first lady of San Francisco started as a co-host of the Fox News evening show, "The Five," having been with the network since 2006. Perhaps because she was spending more time in front of the cameras, Guilfoyle's looks grew increasingly makeup-heavy. Although her era of dramatic cosmetic procedures was still a few years away, by 2012, Guilfoyle's makeup had already taken on a bold and heavy-handed flair. She often appeared with overly vivid touches — flushed bright-pink cheeks, dark eyeliner, glossy lips pushed to excess, and brows darkened with a heavy sweep of powder. The overall effect very much called to mind a beauty queen.

Interestingly, it was in this same year that journalist Liza Mundy published a report in The Atlantic discussing the beauty standards imposed on female anchors for Fox. In her write-up, Mundy reported, "A Fox regular once commented to me that she gets more calls from network management about her hair, clothes, and makeup than about what she says. 'I just think of it as a uniform,' [the journalist] said of her getup." Although it's unclear whether or not Guilfoyle felt any kind of pressure to adhere to these standards, it is important to consider that she was working in a place with an unspoken makeup-heavy rule at the time that she upped her glam.

By the time 2018 came around, Kimberly Guilfoyle was one of the biggest names at Fox. She also appeared to be married to her makeup-heavy look — showing up at numerous events with what seemed to be several layers of foundation caked onto her skin. Although she did leave her television role later that year, Guilfoyle continued to appear in the public eye. That year, she even traveled to Bozeman, Montana, to support then-Republican candidate Matt Rosendale in his bid for the Senate. Close-ups of Guilfoyle's face at Rosendale's campaign events show she was wearing plenty of blush, eyeliner, and eyeshadow. These same shots also revealed that her cheeks and forehead lacked the amount of plasticity typically viewed in unaltered skin.

To understand why Guilfoyle's face looked so frozen, we spoke to Dallas-based board-certified plastic surgeon Dr. Raja Mohan. After examining one of the photos of Guilfoyle's Montana trip, the medical expert posited, "A stiff facial appearance is often the result of overuse of Botox and fillers. In Kimberly Guilfoyle's case, heavy Botox in the forehead and around the eyes, paired with substantial filler in the cheeks, lips, and jawline, can reduce natural movement and create a mask-like effect." Interestingly, Dr. Mohan also concluded that Guilfoyle's makeup might even contribute to this overly smooth look. "Excess volume, combined with heavy makeup or photo retouching, can further exaggerate stiffness," Dr. Mohan told The List.

Kimberly Guilfoyle's face is not the only thing that changed in 2018. During that year, Guilfoyle initiated a relationship with President Donald Trump's son, Donald Trump Jr. Although Guilfoyle and Don Jr. would break up in 2024, there was a time when the two seemed destined to last. Prior to their split, the couple actually had plans to wed.

Fascinatingly, it was during her relationship with Don Jr. that Guilfoyle underwent yet another physical transformation. She began to appear in public with lips that seemed larger than ever before. This was especially evident in a video shared to Guilfoyle's Instagram in May 2024. The footage — which captured Guilfoyle speaking — emphasized the size of her mouth.

Commenting on this in an exclusive conversation with The List, Dr. Raja Mohan attributed Guilfoyle's transformation to fillers. "Kimberly Guilfoyle's lips show signs of significant enhancement, most likely from hyaluronic acid–based dermal fillers. The volume appears evenly distributed throughout both the upper and lower lips, with added definition along the vermillion border and cupid's bow," Dr. Mohan told us. In the surgeon's opinion, Guilfoyle may have undergone multiple procedures, preventing her from moving her lips naturally. "When filler is layered over time, it can lead to a firmer appearance and reduced flexibility, which may explain why her lips move in a more limited way when she talks," explained Dr. Mohan.

In 2025, Kimberly Guilfoyle began a new phase in her career after being nominated by President Donald Trump a year before as the U.S. ambassador to Greece. Although she has long been known for wearing oodles of makeup and pageant-worthy hairstyles, Guilfoyle seemed to ever so slightly tone down her look to reflect her potential new role, just one of the many times Kimberly Guilfoyle tried to look professional but failed miserably.

This was evident on July 9 when she appeared before the Senate Foreign Relations Committee on Capitol Hill during a nominations hearing and was asked questions about Greece's relationship with Turkey. As evidenced by her appearance on the day, Guilfoyle seemed to have taken a small break from some aspects of the bold makeup she's worn in the past, instead wearing a neutral shade of lipstick and a more subtle shade of blush. Although her eye makeup was dark and heavy, she wore glasses, possibly hinting at her desire to be viewed as an intelligent, moral figure. 

This major transition in how Guilfoyle presents her face to the public demonstrates her capacity to shift her image based on different professional situations. While she adopted a more natural look during her tenure in San Francisco politics, Guilfoyle leaned into the beauty-queen style during her time at Fox News. When she dated Donald Trump Jr., Guilfoyle's appearance became more artificially enhanced. In 2025, though, as a possible ambassador, Guilfoyle's face changed once more.